Isobutyric Acid → 2,2,4,4-Tetramethylcyclobutane-1,3-diol

HRID 514651

Reaction equation

HRID 514651 reaction equation
[CH3:1][C:2]1([CH3:10])[C:5](=[O:6])[C:4]([CH3:8])([CH3:7])[C:3]1=[O:9].C(O)(=O)C(C)C>C(OCC(C)C)(=O)C(C)C>[CH3:7][C:4]1([CH3:8])[CH:5]([OH:6])[C:2]([CH3:10])([CH3:1])[CH:3]1[OH:9]

Participants

4

Reactant 2

HCID 6590Isobutyric AcidHCID 136172,2,4,4-Tetramethyl-1,3-cyclobutanedione

Product 1

HCID 763822,2,4,4-Tetramethylcyclobutane-1,3-diol

Reagents, catalysts & solvents 1

HCID 7351Isobutyl isobutyrateSolvent

Procedure

A solution of 18.0 wt % 2,2,4,4-tetramethylcyclobutane-1,3-dione and 3.90 wt % isobutyric acid in isobutyl isobutyrate was added to the reactor system containing 405 mL of a 2 wt % Ru-0.5 wt % Re-0.025 wt % Sn on alumina catalyst at a rate of 20 mL/min. The pressure at the top of the reactor was maintained at 500 psig and the temperature at the top of the catalyst bed was 128° C. These conditions were maintained for 24 hours. The average conversion of the dione was 98.4%. 2,2,4,4-Tetramethylcyclobutane-1,3-diol (16.5 wt %) was obtained at a rate of 24.8 lb/ft3 catalyst/hr (3.50 mmol/g/hr). The average conversion of isobutyric acid was 44.4% (0.592 mmol/g-hr).

Workup

  1. additioncontaining 405 mL of a 2 wt % Ru-0.5 wt % Re-0.025 wt % Sn on alumina catalyst at a rate of 20 mL/min
  2. temperatureThe pressure at the top of the reactor was maintained at 500 psig
  3. customwas 128° C
  4. temperatureThese conditions were maintained for 24 hours

Sources & evidence

ORD record
ord-7f4c092a69464ba78d9ce4582740e4a9
Source dataset
uspto-grants-2015_08
Patent number
US09108895B2

Linked notes

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